40 Questions No One Is Asking You
- Joe Simon
- Aug 13
- 3 min read
Financial Solutions Only You Know the Answers To
Retirement planning is filled with decisions—some simple, others life-altering. Yet many of the most important questions rarely get asked. These 40 questions challenge the way we think about taxes, longevity, Social Security, market risk, and the future of our wealth. Your answers shape your financial story more than any product or investment ever could.
Here are the questions every household should wrestle with:
The 40 Questions
What is the best age to take your Social Security? (74 million Baby Boomers, 66 million Gen Xers — decisions matter.)
Is it possible to make some or all of your Social Security inheritable?
Would you like to know how to make yourself the beneficiary of your own life insurance?
Is there someone at the IRS you love so much that you want to leave them a large portion of your money?
Or someone at a nursing home you adore enough to leave them most—if not all—of your savings?
When the government needs more money, will they get it from the 90% who have none, or the 10% who do?
Where is it written that you must lose 30%, 50%, or even 70% in every market crash to make money?
How many times will you accept those losses before saying enough? Would you be further ahead today if you hadn’t lost money in 2000–2002 or 2007–2008?
Do you want to be rich—or would you prefer an absolute guarantee you will never be poor?
If you lost your job for 30 years, would it hurt your family? Isn’t that essentially retirement?
Do you have enough confidence in your current advisor to seek a second opinion?
Is it fair that when one parent dies, the children may effectively “lose” both parents due to lack of resources?
At 65, you begin the race of “your money vs. your life.” Which one do you want to win?
Doesn’t it take 40 working years to create 80 years of income? How will you accomplish that math?
Was it your intention to make the IRS the primary beneficiary of your IRA, 401(k), 403(b), or 457?
Do you believe another financial crisis like 2007–2008 will happen? What will you do differently this time?
Would you rather be winning by not losing?
Have you heard about filial responsibility laws now being enforced in 30 states?
Did you know the average age of widowhood is 57? And that 80% of husbands die married while 80% of wives die single?
Wouldn’t it be smarter to pay taxes on the way in—so you don’t have to pay them on the way out?
Have you insured your IRA? Did you know that’s possible?
When was the last time you reviewed your beneficiaries?
Have you planned for what happens if your life ends early? What about if it doesn’t?
What’s the safest, easiest way to make your retirement money last longer? Is it eliminating taxes on that income?
How can you turn “forever taxed” money into “never taxed” money?
Are you comfortable going broke slowly?
May I see your after-tax statement?
Stretch IRA rules have existed for 15 years—why haven’t you heard about them?
In 10 years, 100% of your Social Security may go toward healthcare. What pays for food, clothing, and shelter?
If you could stay in complete control of your money until your last breath—and keep it in your family for generations—would you want to know how?
If tax rates rise but revenues can’t, how will that affect you?
Will taxes be higher in the future? Could they be much higher?
Will benefits be lower—higher deductibles, premiums, and out-of-pocket costs? How will you replace them?
If taxes rise and benefits fall, won’t the government print more money? Isn’t that inflation? How do you offset inflation when you’re no longer working?
With higher taxes, lower benefits, and more money printing, won’t volatility increase? How do you protect yourself from the bad volatility and use the good volatility?
If you retire at 65 and die at 70, planning is easy. But if you live to 95 and run out of money at 72—what then?
Do you know the “Rule of 104-12”? Do you know how to use progressive tax law to reduce taxes on fully taxable money?
Do you know the difference between marginal and effective tax rates? Which one actually matters?
Have you learned about the “Power of Zero”?
If someone reached into your wallet regularly, would you stop them? Then why allow the IRS, government, Wall Street, hospitals, or nursing homes to do the same? Wouldn’t controlling that be important?
Now What?
If you reflected honestly on these 40 questions, you’re already ahead of most Americans. Awareness is the first step toward smarter, more strategic financial planning.
For help turning your answers into action:
📩 Contact: js@joesimon.solutions
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